


Undercover Operation

by artemis1967



Category: Supernatural
Genre: Anal Sex, Crossdressing, Dirty Talk, M/M, Public Sex, Rough Sex, Season/Series 12, Undercover Missions, light humiliation
Language: English
Status: Completed
Published: 2018-08-12
Updated: 2018-08-12
Packaged: 2019-06-26 09:31:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,636
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15660474
Author URL: https://archiveofourown.org/users/artemis1967/pseuds/artemis1967
Summary: One of them will have to wear women's clothes during an undercover operation.





	Undercover Operation

 

“Please, Sammy…” His big brother begs once more, doing the best possible imitation of Sam's puppy dog eyes. It doesn’t work, of course.

“You lost on rock-paper-scissors, man. It’s not my fault if you always choose scissors.” Sam tries to hold back the smirk.

“You already have long hair, and I know you tweeze your eyebrows.”

“No.” The negative is immediate, but not very convincing.

“Sammy...”

“Sometimes,” he admits with some embarrassment.

“I knew it.” Dean smiles triumphantly.

“It doesn’t change anything. I've won, and you're going to dress like a woman,” Sam says firmly.

Dean had hated the operation from the start, finding suspicious that Ketch didn’t give more details about it. The member of the British Men of Letters simply sent them a photo of the man they are supposed to observe at a nightclub in North Carolina. Also, he provided documents and clothes necessary for the disguise – a female bartender. According to Ketch, it was the only viable option.

Since then, about an hour ago, the brothers are arguing about who will work undercover. Or rather, they were because Dean chose scissors one more time and lost. Sam wants to roll on the floor laughing when he imagines the scene – his tough big brother dressed as a woman – but his rational mind keeps him quiet; better don’t poke the bear.

“Fine.” Dean finally gives up.

As soon as the bathroom door is closed with a bang, however, Sam lets out the laughter he was holding. _This is going to be fun_ , he thinks.

The image of a tough guy is something that his big brother cultivates from an early age, and even cuddling only happens on rare occasions with all the politics of no chick flick moments. So, this is going to be difficult for Dean and being the pain in the ass little brother that he’s, Sam won’t miss the opportunity to piss Dean off, mainly because if the situation were reversed, he wouldn’t hear the end of it for the rest of his life.

When he manages to control himself, his attention turns to the clothes he will wear and without wasting time he chooses black jeans, a white T-shirt and a leather jacket between the items Ketch sent them. As much as British Men of Letters can’t be trusted, Sam has to admit they are efficient, facilitating the hunt on the technical aspect. The clothes fit perfectly, and he tries to fix his hair before sitting on the bed with his laptop to wait for Dean.

“Dean? Come on, man,” he complains loudly after a while.

“Shut the fuck up, Sam. I don’t know how girls survive this,” Dean yells from the bathroom.

The urge to laugh returns, but Sam restrains himself; he will wait until his brother leaves the bathroom.

“Need help?” He asks, already knowing the answer.

“Of course not, dumbass. You wouldn’t know what to do with this bunch of stuff.”

“Idiot,” Sam mutters, rolling his eyes.

After what seems like an eternity, the bathroom door opens cautiously.

Prepared to mock his big brother, Sam is perplexed by what he sees. The figure coming out of the bathroom doesn’t look like a man, but rather like a stunning woman.

He’s hypnotized immediately by the way Dean bites his lower lip, shiny with lip gloss. The cheekbones are slightly pink, and the green eyes look larger with the mascara perfectly applied. The beautiful face is superbly framed by a wig, the strands a little lighter than Dean's hair, and falling shoulder-length.

His gaze moves down to the black silk top, staring at his brother's new breasts, which don’t look fake or too big. They probably fit very well into Sam's hands.

The mini skirt Dean is wearing is wine and decorated with delicate black embroidery, matching the top. It descends to the middle of his brother's firm thighs, which are covered by black stockings, and stilettos complete the look.

She, or rather he, is beautiful.

When Sam returns to face Dean, he sees the rapid transformation in his expression, going from irritation to playful in a matter of seconds.

“Do you like what you see, little brother?”

Stupid question, he's totally excited by the visual, and the only thing he wants now is to pull Dean against the wall and fuck him senseless.

He clears his throat, trying to find his voice again.

“Hum…interesting, the college boy lost his ability to speak,” he teases, running his tongue deliberately through his full lips.

“Dean...” Sam closes his legs with the intention of hiding his erection, but it's too late, and Dean laughs.

“Little Sammy is excited too.” Now the idiot runs his hands sensuously by the skirt, smiling broadly while he looks at Sam.

Dean’s small spectacle in front of him is the only thing on his mind until the phone rings and the moment is broken. It's Ketch, and Sam answers in a strangled voice.

After the embarrassment of having to assure the British that he’s well, Sam hears the rest of the details of the mission under Dean's smug look.

“Idiot,” is the first thing he says when the phone is turned off.

“You started all this, mocking me when I lost, now you’re gonna have to put up with me!”

Sam quickly gets up from the bed, relieved that his erection is gone. Avoiding further discussion, he merely says, “We have work to do.”

In the bar, Sam plays with his bottle of beer while keeping an eye on his big brother, who has adapted well to work, serving drinks as if he had done it his whole life.

His mood alternates between fun and jealousy every time someone flirts with his brother. Dean's disgusted face is adorable, and he smiles when it happens. On the other hand, the guys’ lascivious looks to his brother's ass, when Dean turns around, make Sam's blood boil and want to throw some punches, which is strange because he's rational usually, rarely acting like a jealous boyfriend. Dean often plays this role.

Sometime later, Ketch calls canceling the operation because the police caught the suspect. He puts the phone in his pocket and looks at his brother, still fantastic in women's outfit. Not knowing when he's going to get another chance like this, he decides to wait a little longer, fantasizing dirty things he wants to do with Dean dressed like that.

The interlude lasts until he sees his big brother put a beer on the counter with force, the anger visible in his features. The combined signal between them tells Dean the operation is over. Immediately he sees his brother holding a man by the collar, but he can’t hear what Dean says; it works, and the guy throws some notes on the counter, leaving the bar practically running.

With the same usual cocky look, Dean talks to a woman before leaving his post. The swing of his hips calls the attention of several men on his way to the exit, and Sam stands up determined, it's time to put his provocative big brother in his place.

Nevertheless, there is no sign of Dean in the parking lot, and he hurries to the Impala.

“Dean?” He calls, looking in through the window. Empty. _Where the hell is he?_ Worry hits him, and the worst scenarios form in Sam’s head. With Dean dressed that way, it's easy to attract the wrong kind of attention.

He notices the alley and starts to walk there. From the corner of his eyes, he sees a big shape coming out from behind a car but can’t react in time, only grunting when he’s slammed into the wall. A familiar voice warns, “Shhh, it's me.”

“Dean? What the hell, man!”

With the stilettos, Dean is taller than him, which is both strange and exciting at the same time; his brother's erection fits perfectly against his ass without Sam having to open his legs.

Besides that, even fully dressed, he can feel the difference in the texture of his brother's clothing – it’s softer. This and Dean's new hair on his neck are doing wonders for his libido, and his dick starts to thicken.

“I’ll fuck you here, where everyone can see us.”

“What? Are you crazy, Dean?” His rational mind fights to take control, which is difficult when he feels a hand caressing his cock over his jeans.

“Fuck, Dean!”

“Calm down, we'll get to that part,” Dean says, hot breath in his ear and firm body pressed against him from shoulder to dick; Sam pushes back, rubbing his ass on his brother's hard member.

His hands are positioned against the wall. Then he feels his belt being unbuckled and the zipper of his jeans coming down quickly. The warm body pulls away from him momentarily, and the cold air in contact with his skin causes chills when his jeans and underwear are worked down until they settle down to his ankles.

Before he can protest at the excessive exposure – releasing only his ass is more than enough to fuck – he feels a leg between his, the softness of the stocking practically caressing the sensitive skin inside his thighs. Also, he can feel the texture of Dean's skirt against his ass, perfectly shaping the long cock under it.

Dean's hot tongue begins to draw patterns on his neck, and he's already hard as steel, pre-come forming wet spots on his white T-shirt. He forgets all about the lack of clothes in public.

“Did you think things would change between us because I'm dressed as a woman?” The question surprises him, and he gasps when his ass cheeks are opened, the hot and hard cock rubbing between them. He can still feel the soft fabric against his skin and thinks Dean must have just pulled the clothes off enough to free his dick.

“That I would open my legs like a good girl and take it without complaining?” Dean forces his body against Sam, demanding an answer.

“No…” The word is strangled from his throat, more like a yes. And even if he doesn’t admit it out loud, that is precisely what he thought. But his big brother knows him very well, and he probably didn’t believe Sam anyway.

The delicious friction against his hole ends, and he whimpers when feels a lubed finger being inserted quickly into him. Soon two fingers are roughly working him open, and he closes his eyes enjoying the contact with his prostate. Another lick on his neck and a third finger is added, causing tremors in his body. He’s more than ready and moves his hips, signaling to his big brother exactly that.

Understanding the message, Dean pulls his fingers out, pushing his erection slowly until he's fully inside while Sam spreads his legs, trying to accommodate it. The member invading his interiors is huge, and even though his body knows this after years, he still feels engulfed by a wave of desire and fullness. It's like he's burning out from the inside.

The first impulses are slow, but it doesn’t take long before Dean starts fucking him hard and fast, forcing Sam up the wall with each thrust of his hips. The cock pulsing inside him always reminds Sam how much he likes it, how well his big brother knows him and what he needs.

“You were begging for it. I call the shots, man, never forget it again,” his brother growls, shoving increasingly deeper, hard and rough.

The only thing Sam can do is groan in agreement, his incoherence a direct result of his big brother’s impulses nailing his prostate, sending a rush of pleasure right to his nucleus; it feels so fucking amazing.

The grip on his waist is strong, and even without looking he knows that bruises are starting to form. Marked and owned by his big brother dressed like a woman, and in public. Even in his darkest fantasies, Sam couldn’t have imagined anything like this.

He likes. Immensely.

All of a sudden, Dean pulls out entirely, pushing back in slowly; sweat is dripping off his forehead and neck, and Dean licks a trail from his ear down his neck, and it’s dirty and libidinous.

A warm hand wraps around his dick, stroking it in time with the movement of Dean’s hips. The synchrony is perfect, and Sam gets lost in the sensations.

Now each thrust is vicious, burying the long and thick member entirely in Sam's body. The noise of sex echoes through the night, and Sam thinks it's a miracle they haven’t been detected yet.

He arches back against the solid body, moaning with every touch of his brother’s big cock. At the same time, he tries to hold himself to avoid being crushed against the wall, especially when the other man picks up the rhythm, his impulses lifting Sam onto his toes.

Sam’s close, practically falling apart under his big brother’s ministrations, who is murmuring obscene words into his ear. Time ceases existing for Sam until he screams out in ecstasy when he comes, throwing his head back, cock pulsating in waves and ass contracting around the thick circumference inside him.

Dean grunts, following him after a few powerful thrusts and emptying his come into Sam’s interiors, filling him completely.

A round of applause and whistles scare the two men, and they look at the source of the noise. There is a small crowd of people just outside the doorway of the bar. Probably they have witnessed everything.

“Congratulations, ma'am! It's always good to see a lady put a man in his place.” He hears a male voice say.

Deadly embarrassed, Sam stares back at the wall, feeling his face burning. He can’t help a shudder when his brother pulls out of him, yet he doesn’t move.

“Put your clothes on, Sammy, fast,” his brother says before turning to the crowd, hiding Sam while he pulls his clothes back.

“Well, I think he learned his lesson, guys. There's nothing else to see here.” Dean's voice is steady, and the sound of some disappointed voices is followed by the noise of movement back to the bar.

It's all so surreal and anticlimactic that Sam comes back to himself when his aching ass touches the passenger seat. The groan is inevitable, and he looks at his brother accusingly, who, by the way, is still perfectly composed in women's clothes. Which is unfair because Sam feels wholly fucked out.

“I've never been so ashamed in my life, Dean.” His face is burning again.

“Forget that. We've provided a show for them anyway.”

Impossible to put any reason in his brother’s hard head when he has that look of who is proud of himself. Any of these days Dean's exhibitionism will put them in trouble.

“Exhibitionist. And did you have to be so rough?” The pain in Sam’s body is becoming very well-known now.

“Well, as that guy out there said, you needed to learn how to treat a lady,” Dean mocks. “And I saw when Ketch called, but you chose not to say anything.”

“I…” He stutters.

“Don’t even try to justify yourself, Sam,” he interrupts his brother, then adds, “Lucky for you that I had a lot of fun.”

_At least Dean wasn’t the only one who had a lot of fun_ , he smiles to himself, pleased.

Jerk.”

“Bitch.” It’s the automatic response.

Dean starts the Impala, and Sam collapses against the seat, tired, aching and uncomfortably wet, but the only thing that goes through his mind is the beauty of his brother dressed like a woman.

He presses his head to the passenger’s side window and closes his eyes; the last thing he thinks before succumbing to sleep is that he will try to convince Dean to wear feminine clothes for him again.


End file.
